1. Conversation Openers
Questions to begin a conversation with anyone in the organization
What’s most important to you in your job? . . . What do you enjoy most? . . . What are you best at?
When you think about your personal mission in your work, what are you most hoping to contribute?
What’s most challenging? . . . What is frustrating you the most? . . . What do you worry about?
What challenges is your _____ [hospital/university/city/organization] facing?
How are you addressing those challenges? . . . What else would help?
When you think about things that are constraining you at work, what would you remove first if you could?
What is changing in your job responsibilities? . . . What does that mean for you? . . . What will your work look like 1 year from now?
If you could change anything about what you do, what would it be? . . . What else? . . . What else?
What do you have to wait for in your work? . . . What holds you up or frustrates you? . . . What do you always have to look for?
How do you see your _____ [organization/department/group/customers/supply chain] evolving over the next 12-18 months?
One year from now, when you look back, what will you be glad you focused on today?
What originally prompted you to take this meeting?
Tell me about a big success you or your team recently accomplished. What would it take to make that happen more often?
Who do you talk to most at work? What is the purpose of talking to them?
Which other [organization like yours] are you trying to emulate and why? . . . What professionals in your sphere do you always listen to?
When you sit down with old friends, what do you tell them you are hoping to do and what you are hoping your business will do?
Questions to help find worthwhile additional contacts
Who else do you think I should talk with?
Who else is coping with this issue? . . . Would you introduce me to them?
If you need to buy something big, complex and expensive for work, how does that happen? . . . Who else has to be involved? . . . How long does it typically take?
If the thing you need is really outside your area of job responsibility, how do you get the organization to agree to it?
What role in your department is most involved in evaluating large projects?
STRATEGIC OPPORTUNITY: Questions
Questions to gain an understanding of the Current Situation, Issues, Facts, or Profile Points
Temporary Advantage Customer’s Project or Problem Quantifiable Business Metric Customer’s Goals & Objectives Customer’s Political Agenda
What other options are you
considering?
What challenges is your _____
[hospital/university/city/
organization] facing?
What will be different 1-2 years
from now if you move this
project forward?
What do you most want to
integrate into your work this
year? . . . What would that do
for you?
Who would be a great person
to work with more if you had
more time?. . . Why?
What is working for you now? What is your attention focused
on? . . . What projects are
consuming your time?
What key metrics will this effort
affect?
If you could get help to
accomplish a significant goal,
what would it be?
Who should be / Who is on the
evaluation team? . . . What do
you think of that team?
What do you find most
interesting about the solution
we are offering?
What’s changing in your
industry? . . . At your company?
What is the biggest impact
from this project that you plan
to track?
What would take your
department or organization to
"the next level"?
Who are you worried might
have a different perspective on
this than you do?

2. STRATEGY: Target Acquisition Questions
WHY – will this decision be made?
1 NEED
• Problem I talked to a customer recently, similar to you, that is having a problem with______. What are you facing in that area?
• Project How are you addressing that issue? How do you plan to address that challenge? What else would help?
2 TIMING
• Date Regarding this challenge, what would you expect to have resolved 6 months from now? 12 months? 18months?
• Compelling Mechanism What is motivating this project now? What is at risk if you don’t move forward? What regulations are affecting this issue?
3 MONEY
• Financial Position In what ways is the organization’s financial situation shaping this project and decisions associated with it?
• Funding Status How will the budget be created for this? Tell me a little bit about the budget you have for this initiative.
4 VALUE
• Quantitative What metrics are you concerned about in this area? How will you measure the success or failure of the solution you chose?
• Qualitative What intangible results do you expect from this project? What will be most valuable to your customers/employees?
HOW – will this decision be made?
5 CRITERIA
• Technical How will you evaluate if the technology will satisfy your needs? What do you expect to see the technology do?
• Business How will the purchase be justified? What analyses will you rely on to make the decision? Which of those are most important?
6 RESOURCES
• Ours What do you need from us? How can we best support your efforts?
• The Customer’s What will need to happen to move this initiative forward? What internal resources must come into play here?
7 PROCESS
• Events Give me an overview of how you see this rolling out. How does the RFP get written? What committee meetings must occur?
• Timeline What does the timeline for this project look like? What might possibly delay this project?
8 EXECUTION
• Implementation What will be most important during implementation? What has caused trouble during implementation of projects in the past?
• Risks What do you see as the risks of having a solution like the one we’ve been discussing? What are the risks of not having it?
WHO – will really make (drive) this decision?
9 HIERARCHY
• Decision Makers Who must agree to the solution in order for it to move ahead? Who else?
• Approvers Who is making recommendations to the decision makers?
10 SUPPORT
• Inside Support Who originally brought this idea forward? Who is a change agent, perhaps a bit of a maverick here?
• Criteria & Process How will the people supporting this effort evaluate the options?
11 EXECUTIVES
• Access What information or conversations do key stakeholders need to make their decisions?
• Credibility What would really impress your leaders? What are your highest-level people expecting to see to make this decision?
12 POLITICAL
• Power Where are the unexpected influences going to come from? Who is everyone going to listen to?
• Philosophy How will the team evaluate the offerings? What is the political culture like here?